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. 2020 Oct 22;11(48):13071-13078.
doi: 10.1039/d0sc02947e.

Silyloxymethanesulfinate as a sulfoxylate equivalent for the modular synthesis of sulfones and sulfonyl derivatives

Dae-Kwon Kim  1 , Hyun-Suk Um  1 , Hoyoon Park  1 , Seonwoo Kim  1 , Jin Choi  1 , Chulbom Lee  1
Affiliations

Silyloxymethanesulfinate as a sulfoxylate equivalent for the modular synthesis of sulfones and sulfonyl derivatives

Dae-Kwon Kim et al. Chem Sci. .

Abstract

An efficient protocol for the modular synthesis of sulfones and sulfonyl derivatives has been developed utilizing sodium tert-butyldimethylsilyloxymethanesulfinate (TBSOMS-Na) as a sulfoxylate (SO2 2-) equivalent. TBSOMS-Na, easily prepared from the commercial reagents Rongalite™ and TBSCl, serves as a potent nucleophile in S-alkylation and Cu-catalyzed S-arylation reactions with alkyl and aryl electrophiles. The sulfone products thus obtained can undergo the second bond formation at the sulfur center with various electrophiles without a separate unmasking step to afford sulfones and sulfonyl derivatives such as sulfonamides and sulfonyl fluorides.

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Conflict of interest statement

D.-K. Kim, H.-S. Um, H. Park, and C. Lee are inventors on patent application 10-2019-0126427 (Republic of Korea) submitted by Seoul National University that covers the modular synthesis of sulfones and sulfonyl derivatives using TBSOMS-Na.

Figures

Scheme 1
Scheme 1. Synthetic strategies for installing sulfonyl units.
Scheme 2
Scheme 2. One-pot synthesis of unsymmetrical sulfones.
Scheme 3
Scheme 3. Application of the sulfoxylate strategy for the modular synthesis of sulfonyl derivatives.
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